The Afternoon Paper Boy

As a teen Jimmy routinely looked in windows wherever he walked or drove. If he saw something moving behind the shade, he would stop and look. He tried to be oh, so, casual about this.

Jimmy would start to get hard almost as soon as he saw the least revealing of flesh. He had remedy for this. He would masturbate until he got home, holding back on coming and keeping his penis hard.

Sometimes he would unzip his pants and pull his stiff penis out of his briefs. He would then conceal his hard on with his coat or his paperboy’s bag. On other occasions he would pull his briefs down by maneuvering his hands through his pockets and feel his penis rub against his pants, tenting them out in front. If he could find bushes to hide in or an area that he thought he could be concealed in he would take off his pants and walk around with his dick hanging out for all to see.

Now, Jimmy was very cautious. He knew that if he were to be caught looking in windows or with his penis out, the punishment would be severe. He didn’t want to have a record as an exhibitionist, so he used discretion at all times. He would look all around to see if there was anyone in sight. He would wait, and this anticipation would cause his erection to grow even larger. When he was sure that it was just him and the night air, or him and the bushes covering him, or him alone in the woods, he would let loose his penis.

Of course, there were a couple of close calls. Once while delivering newspapers – he had an afternoon newspaper route, he caught a glimpse of a 25-year-old female customer coming out of the shower. He had a good angle on this. She lived in a basement apartment and he had five steps down to her landing. He spotted her while he was on the top step.

She was dark haired and had, in Jimmy’s mind, a terrific body. She often would stop him and talk to him about what he liked to do, what school was like, what he planned to do after school, Friday’s game, and many other topics. Once or twice she had offered him something to drink and she had continued to talk. She always was dressed in a t-shirt or a sweater and jeans. Nothing revealing. But Jimmy could see her figure underneath whatever it was she wore.

A few days before, Jimmy had seen her from this step as she went from the bath to the bedroom in her underwear. It was a very quick glance, but his guesses about her breasts and her ass were confirmed. She had full white panties and a lace bra on that time. Jimmy had become erect at once. He did nothing about it then. He put her paper in between the screen door and the door as she had requested and moved on. Later, at home in bed, he replayed the scene in slow motion, and recalled every frame. He stroked his penis as the scene played in his mind and came, shooting cum up his chest and catching his chin with his own crème.

The next day she was waiting for him when he delivered the paper. She asked him if he had seen anything moving in the apartment when he delivered the paper the day before. Jimmy stammered a little, looked away, and said, “No, I didn’t see anything really. Just a shadow moving, that’s all. Looked up when the light changed.”

Today, he was sure that he saw her wrapped in a towel, moving from the bathroom to the bedroom again. He immediately was hard. Following his usual caution, he looked to see if there was anyone around. Satisfied that he was alone, he unzipped his fly, took out his penis and placed his paper delivery bag in front of him. Then he stood and looked in the glass window on her door. He waited patiently for another glimpse. He was not disappointed.

She had gone into the bedroom, he guessed. He was ready to put the paper between her screen door and her door when she emerged from the bedroom totally nude and walked into the kitchen. He saw her 38C breasts. Huge nipples! Large aureoles surrounding them He looked down and saw her waist. Her hips. And her pussy fully covered with black curls.

Jimmy’s heart picked up. His penis throbbed in the air. He reached for it and began to stroke its full length.

Just then he realized she might see him. She was in the kitchen a few feet away. He was by the screen door, penis in his hand, eyes glued to her body. If she looked out the window she would see his face staring in. Would she report him? He couldn’t help but to stroke his penis and stroke it and stroke it, varying the pressure, pulling it tight at the tip. She turned away from the window and Jimmy was afforded an incredible view of her ass.

Jimmy loved looking at women’s asses. He dreamed of the day that he could kiss checks and insert his tongue into some girl’s butt. He wanted to hold and hang on to the cheeks that were in front of him.

She turned away from the kitchen cabinet and Jimmy once more had a full frontal view. He had hungered for an opportunity to suck someone’s nipples. He had seen his sisters. He would soon see many others. But this was the first nude woman he had seen outside of his family.

When she turned to him he saw her black curls and fully covered mound. He had seen pictures like this in his father’s nudist magazines. He grew short of breath. Grabbing his penis in his hand once more he came. He spurted white hot cum all over his news delivery bag.

Weak kneed he could have sworn he saw a smile on her face as she left the kitchen and returned to the bedroom out of sight. Maybe he imagined it.

With a satisfied smile and lightness now in his shorts, Jimmy zipped up and continued with his route. He had to figure a way to clean his bag before he got home.